| Identification | Back Directory | [Name]
5-Aziridino-2,4-dinitrobenzamide | [CAS]
21919-05-1 | [Synonyms]
CB-954
CB-1954
NSC 115829
tretazicar
CB 1954;CB-1954
Tretazicar (>
Tretazicar (>94%)
CB1954(TRETAZICAR)
Tretazicar (CB 1954)
5-Aziridino-2,4-dinitrobenzamide
2,4-Dinitro-5-ethyleneiminobenzamide
5-(1-aziridinyl)-2,4-dinitrobenzamide
5-(Aziridin-1-yl)-2,4-dinitrobenzamide
2,4-Dinitro-5-(aziridine-1-yl)benzamide
Benzamide, 5-(1-aziridinyl)-2,4-dinitro-
5-(1-Aziridinyl)-2,4-dinitrobenzamide, 5-(Aziridin-1-yl)-2,4-dinitrobenzamide | [Molecular Formula]
C9H8N4O5 | [MDL Number]
MFCD00869490 | [MOL File]
21919-05-1.mol | [Molecular Weight]
252.18 |
| Chemical Properties | Back Directory | [Melting point ]
173 °C | [Boiling point ]
427.2±45.0 °C(Predicted) | [density ]
1.671±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Acetonitrile (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
solid | [pka]
14.23±0.50(Predicted) | [color ]
Yellow to Dark Yellow | [InChI]
1S/C9H8N4O5/c10-9(14)5-3-7(11-1-2-11)8(13(17)18)4-6(5)12(15)16/h3-4H,1-2H2,(H2,10,14) | [InChIKey]
WOCXQMCIOTUMJV-UHFFFAOYSA-N | [SMILES]
NC(=O)c1cc(N2CC2)c(cc1[N+]([O-])=O)[N+]([O-])=O |
| Hazard Information | Back Directory | [Description]
CB-1954 is a prodrug that is enzymatically activated to generate an antitumor agent that forms DNA-DNA interstrand crosslinks. In rat Walker 256 carcinoma cells, CB-1954 is reduced by NAD(P)H:quinone oxidoreductase (NQO1) to the cytotoxic derivative 5-(aziridin-1-yl)-4-hydroxylamineo 2 nitrobenzamide, a bifunctional alkylating agent. | [Uses]
5-Aziridino-2,4-dinitrobenzamide is an anticancer prodrug used in gene therapy research and is known to be activated by NAD(P)H Quinone Oxidoreductase 2.
| [Biochem/physiol Actions]
CB 1954 is an anticancer prodrug used in gene therapy research; activated by NAD(P)H quinone oxidoreductase?2. | [in vivo]
Tretazicar (CB 1954) (80 mg/kg; i.p. on days 2 and 9) results in a significant increase in survival[3]. | Animal Model: | Female BALB/c mice (AB22-nr, SKOV3 human ovarian tumour xenograft)[3] | | Dosage: | 80 mg/kg | | Administration: | i.p. on days 2 and 9 | | Result: | The median survival of the AB22-nr was 49 days. Resulted in a significant increase in survival. |
| [storage]
Store at -20°C | [References]
[1] R J KNOX. Bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by human NAD(P)H quinone oxidoreductase 2: a novel co-substrate-mediated antitumor prodrug therapy.[J]. Cancer research, 2000, 60 15: 4179-4186.
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